Rearrangement of alkynyl sulfoxides catalyzed by gold(I) complexes

Journal of the American Chemical Society

Volumn 129, Issue 14, 2007, Pages 4160-4161

  Shapiro, Nathan D ^a   Toste, F Dean ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNYL GROUP; GOLD; SULFOXIDE;

ARTICLE; BIOTRANSFORMATION; CATALYSIS; CATALYST; CYCLIZATION; FRIEDEL CRAFTS REACTION; ISOMERIZATION; QUANTUM YIELD; REACTION ANALYSIS;

ALKYLATION; CATALYSIS; GOLD; MOLECULAR STRUCTURE; SULFOXIDES;

EID: 34247154915     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja070789e     Document Type: Article

References (40)

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26. The less reactive diastereomer of (±)-12 (characterized by X-ray crystallography; see Supporting Information) proceeded to only 15% conversion after reaction at 35°C for 24 h.
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32. 1. (Chemical Equation Presented)
33. Homopropargyl sulfoxide 36, in which the ortho-positions of the aromatic ring are substituted, rearranged to enone 37 via a proposed mechanism involving a 1,2-H shift of the intermediate carbene. (Chemical Equation Presented)
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37. The use of cationic phosphinegold(I) complexes as catalysts led to drastically reduced yields. The use of AuCl as a catalyst for reaction conducted at high concentrations led to formation of dimer 38 along with disulfide 39. (Chemical Equation Presented)
38. See Supporting Information for additional examples.
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40. The lack of sulfide cross-over in the gold-catalyzed rearrangement of 27b and 27c is consistent with an intramolecular sulfide shift. (Chemical Equation Presented)